Premium
Diastereoselective Radical Tandem Addition‐Cyclization Reactions of Aromatic Tertiary Amines by Semiconductor‐Sensitized Photochemical Electron Transfer
Author(s) -
Marinković Siniša,
Hoffmann Norbert
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400102
Subject(s) - chemistry , tandem , photochemistry , electron transfer , deuterium , photocatalysis , photoinduced electron transfer , radical cyclization , radical , semiconductor , homogeneous , radical ion , organic chemistry , catalysis , materials science , physics , quantum mechanics , composite material , thermodynamics , ion
The diastereoselective radical tandem addition‐cyclization reaction of N , N ‐dimethylaniline ( 2 ) with menthyloxyfuranone 1 was initiated by photochemically induced electron transfer using inorganic semiconductors (TiO 2 , ZnS, SiC and SnO 2 ) as sensitizers. The rearomatization step, which also causes the partial reduction of 1 , was studied by isotopic labeling experiments using deuterated derivatives of 2 . The influence of the semiconductor surface on these processes has been characterized and compared with the results obtained under homogeneous conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)